Common NameNadph
Descriptiontrue
Structure
Molecular FormulaC21H30N7O17P3
Average Mass745.42090
Monoisotopic Mass745.09110
IUPAC Name{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2s,3s,4s,5s)-2-(6-aminopurin-9-yl)-5-{[({[(2s,3r,4s,5s)-5-(3-carbamoyl-4h-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry Number53-57-6
SMILESNC(=O)C1=CN([C@@H]2O[C@H](COP(=O)([O-])OP(=O)([O-])OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)([O-])[O-])[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
InChI IdentifierInChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChI KeyACFIXJIJDZMPPO-NNYOXOHSSA-N
CHEBI IDCHEBI:57783
HMDB IDHMDB0000221
Pathways
NameSMPDB/PathBank
Glutathione metabolism
One carbon pool by folate
beta-Alanine metabolism
Fructose and mannose metabolism
Lysine degradation
pentose phosphate pathway
Pyruvate metabolism
Purine metabolism
Tyrosine metabolism
Starch and sucrose metabolism
Pyrimidine metabolism
Primary bile acid biosynthesis
Tryptophan metabolism
Nicotinate and nicotinamide metabolism
Arginine and proline metabolism
Pterine Biosynthesis
Steroid Biosynthesis
Glycerolipid Metabolism
Histidine metabolism
Fatty Acid Elongation In Mitochondria
Ubiquinone Biosynthesis
Androgen and Estrogen Metabolism
Glutamate Metabolism
Retinol Metabolism
Arachidonic Acid Metabolism
Piroxicam Action Pathway
Ibandronate Action Pathway
Simvastatin Action Pathway
Acetylsalicylic Acid Action Pathway
Etodolac Action Pathway
Ketoprofen Action Pathway
Ibuprofen Action Pathway
Rofecoxib Action Pathway
Pravastatin Action Pathway
Rosuvastatin Action Pathway
Diclofenac Action Pathway
Sulindac Action Pathway
Alendronate Action Pathway
Celecoxib Action Pathway
Ketorolac Action Pathway
Lovastatin Action Pathway
Suprofen Action Pathway
Bromfenac Action Pathway
Indomethacin Action Pathway
Meloxicam Action Pathway
Zoledronate Action Pathway
Mefenamic Acid Action Pathway
Cerivastatin Action Pathway
Risedronate Action Pathway
Oxaprozin Action Pathway
Nabumetone Action Pathway
Valdecoxib Action Pathway
Pamidronate Action Pathway
Fluvastatin Action Pathway
Naproxen Action Pathway
Glucose-Alanine Cycle
Steroidogenesis
Atorvastatin Action Pathway
2-Hydroxyglutric Aciduria (D And L Form)
5-Oxoprolinuria
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Alkaptonuria
Beta Ureidopropionase Deficiency
Dihydropyrimidinase Deficiency
Gamma-Glutamyltransferase Deficiency
Glutaric Aciduria Type I
Glycerol Kinase Deficiency
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)
Hawkinsinuria
Histidinemia
Leigh Syndrome
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)
Molybdenum Cofactor Deficiency
Prolidase Deficiency (PD)
Prolinemia Type II
Hypercholesterolemia
Purine Nucleoside Phosphorylase Deficiency
Pyruvate Dehydrogenase Complex Deficiency
Tyrosinemia Type I
UMP Synthase Deficiency (Orotic Aciduria)
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Saccharopinuria/Hyperlysinemia II
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Diflunisal Action Pathway
Congenital Bile Acid Synthesis Defect Type II
Cerebrotendinous Xanthomatosis (CTX)
Zellweger Syndrome
Familial Hypercholanemia (FHCA)
Congenital Bile Acid Synthesis Defect Type III
Lysosomal Acid Lipase Deficiency (Wolman Disease)
Phenytoin (Antiarrhythmic) Action Pathway
Lidocaine (Antiarrhythmic) Action Pathway
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Vitamin A Deficiency
Glutathione Synthetase Deficiency
Hyperinsulinism-Hyperammonemia Syndrome
Metachromatic Leukodystrophy (MLD)
Globoid Cell Leukodystrophy
Gaucher Disease
GABA-Transaminase Deficiency
Leukotriene C4 Synthesis Deficiency
17-Beta Hydroxysteroid Dehydrogenase III Deficiency
Hyperprolinemia Type II
Hyperprolinemia Type I
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)
Ornithine Aminotransferase Deficiency (OAT Deficiency)
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency
Homocarnosinosis
Desmosterolosis
CHILD Syndrome
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)
Smith-Lemli-Opitz Syndrome (SLOS)
Lidocaine (Local Anaesthetic) Action Pathway
Imipramine Action Pathway
Desipramine Action Pathway
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Disulfiram Action Pathway
Thioguanine Action Pathway
Nicotine Action Pathway
Methotrexate Action Pathway
Cyclophosphamide Action Pathway
Ifosfamide Action Pathway
Ethanol Degradation
Phytanic Acid Peroxisomal Oxidation
Vitamin K Metabolism
Transfer of Acetyl Groups into Mitochondria
Tamoxifen Action Pathway
Plasmalogen Synthesis
Dopa-responsive dystonia
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiency
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)
Hyperphenylalaninemia due to dhpr-deficiency
Segawa syndrome
Sepiapterin reductase deficiency
Ureidopropionase Deficiency
Carnosinuria, carnosinemia
Tyrosinemia, transient, of the newborn
Dopamine beta-hydroxylase deficiency
5-oxoprolinase deficiency
Gamma-glutamyl-transpeptidase deficiency
Creatine deficiency, guanidinoacetate methyltransferase deficiency
Hyperornithinemia with gyrate atrophy (HOGA)
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]
L-arginine:glycine amidinotransferase deficiency
Cholesteryl ester storage disease
Hyper-IgD syndrome
Mevalonic aciduria
Wolman disease
Xanthinuria type I
Xanthinuria type II
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
Fabry disease
Krabbe disease
Hyperlysinemia I, Familial
Hyperlysinemia II or Saccharopinuria
D-glyceric acidura
Familial lipoprotein lipase deficiency
Monoamine oxidase-a deficiency (MAO-A)
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
Fructosuria
Aromatase deficiency
17-alpha-hydroxylase deficiency (CYP17)
Succinic semialdehyde dehydrogenase deficiency
Pyridoxine dependency with seizures
11-beta-hydroxylase deficiency (CYP11B1)
21-hydroxylase deficiency (CYP21)
Corticosterone methyl oxidase I deficiency (CMO I)
Corticosterone methyl oxidase II deficiency - CMO II
Ibuprofen Metabolism Pathway
Cyclophosphamide Metabolism Pathway
Ifosfamide Metabolism Pathway
Tamoxifen Metabolism Pathway
Lidocaine (Local Anaesthetic) Metabolism Pathway
Imipramine Metabolism Pathway
Desipramine Metabolism Pathway
Nicotine Metabolism Pathway
Felbamate Metabolism Pathway
Carbamazepine Metabolism Pathway
Valproic Acid Metabolism Pathway
Clomipramine Metabolism Pathway
Doxepin Metabolism Pathway
Nevirapine Metabolism Pathway
Celecoxib Metabolism Pathway
Doxorubicin Metabolism Pathway
Rosiglitazone Metabolism Pathway
Warburg Effect
Antipyrine Action Pathway
Antrafenine Action Pathway
Carprofen Action Pathway
Etoricoxib Action Pathway
Fenoprofen Action Pathway
Flurbiprofen Action Pathway
Magnesium salicylate Action Pathway
Lumiracoxib Action Pathway
Lornoxicam Action Pathway
Phenylbutazone Action Pathway
Nepafenac Action Pathway
Trisalicylate-choline Action Pathway
Tolmetin Action Pathway
Tiaprofenic Acid Action Pathway
Tenoxicam Action Pathway
Salsalate Action Pathway
Salicylate-sodium Action Pathway
Salicylic Acid Action Pathway
Acetaminophen Action Pathway
Apparent mineralocorticoid excess syndrome
3-Beta-Hydroxysteroid Dehydrogenase Deficiency
2-aminoadipic 2-oxoadipic aciduria
27-Hydroxylase Deficiency
Folate malabsorption, hereditary
Fructose intolerance, hereditary
The oncogenic action of 2-hydroxyglutarate
The Oncogenic Action of Succinate
The Oncogenic Action of Fumarate
Glutaminolysis and Cancer
The oncogenic action of L-2-hydroxyglutarate in Hydroxygluaricaciduria
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria
Androstenedione Metabolism
Estrone Metabolism
StateSolid
Water Solubility5.45e+00 g/l
logP-1.13
logS-2.14
pKa (Strongest Acidic)0.66
pKa (Strongest Basic)4.92
Hydrogen Acceptor Count18
Hydrogen Donor Count9
Polar Surface Area364.15 Ų
Rotatable Bond Count13
Physiological Charge-4
Formal Charge0
Refractivity153.87 m³·mol⁻¹
Polarizability60.22

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